dear m

1

[Probably some time mid April 2023]

A month of making out, a few weeks of second base, and days of failed attempts at reaching for his dick led to the now.

It was apparent that still, even after craving this for so long, the thought scared me. Not typical paranoia you would expect, but what I was really nervous about was the milestone. I am those kind of people.

Last day of school, first kiss, first time touching a dick. All very important to me. I didn't want to mess up my first time.

I had gotten somewhat there before, tracing my fingers along the top of his waistband and just barely breaking the seal of his underwear with the tip of my pinky, while the rest of my hand laid on his stomach. It was all intentional. I could tell he was getting increasingly frustrated with this the longer I did it.

Never did I cross that threshold and move further to the front of his pants, over the bulge that I could see from looking down at his dick pushing against his pants. It didn't help that he wore sweatpants 90 percent of the time.

But the past few days have been different. The almost daily hour long make out sessions in the backseat of my car hinted at more than second base and tummy rubbing.

We would lie comfortably in the back of my small Honda- knees slightly bent but nothing too crazy. After practice, he carried his big dufflebag from the track to my car so we could lodge it between the back of the passengers seat and the backseat cushion to extend it.

I rested my body slightly on top of the left part of his body (he always sat on his bag so I got the more comfortable side), one arm under eachother with a free hand out to roam each others bodies.

It was this particular day I had a craving for more. During our usual afternoon car hookups the day before, I had accidentally trailed just slightly too far down underneath his pants. My fingers strung the tent his dick made in his underwear, a moment it wasn't being held down by the terribly constricting waistband of his sweats. His dick was fully sprung up under the thin and smooth fabric from his underwear, and it could feel how hard he was just from the tension of it being pulled away from the rest his body. My fingers never even once grazed him, but imagining a more comprehensive print of his dick without the sweats on under that thin fabric was enough to have kept me up the night before with one hand in my panties and the other holding his cologne drenched crewneck over my face.

The idea of third base had been floating between us for some time, always when I would allude to wanting to go for it and waiting for some sign of reciprocation from him.

I would ask if he 'wanted me too' ,

he would always just reply 'sure' .

Indecisive, almost impartial to the idea of it. I wasn't sure what to make of it, if he was nervous, didn't want to pressure me, or didn't want me to at all. I guess now that being hard in the first place should've debunked this, but I still met that possibility wander in my mind.

My fingers strung down from cupping his face when kissing, to his neck, to his chest, and down at that area much quicker than I typically would've a day before- I wanted to get into things.

I barely rested my hand directly top of it, almost looking for some kind of reaction from him. Getting his dick touched for the first time probably wasn't as big of an event in his mind as it was in mine. I couldn't feel much other than the outline of his dick under the bend of my fingers. I was almost cupping it awkwardly, too nervous to move my hand at all.

He was hard. Really hard. Way different than I imagined it being. Only allowing myself partial exploration of his dick under the stiff posture of my fingers only made me more and more desperate to touch him. The position of my hand softened over his dick almost immediately.

I let my fingers trace up and hit the bottom edge of his tip, clearly differentiating it from the rest of his dick. Then I let them form together again, as I felt the very top of his dick. Still applying little to no pressure, and only feeling the fabric of his sweats against my fingertips.

I was subconsciously painting a picture of his dick under his clothes in my mind from what I was feeling. The thickness, rounded edge of his tip and imagining if my touch was enough to form a small patch of precum near the band of his underwear.

I reached down again, past his tip, trying hard to maintain my composure in the kiss while I have my way with his body. I could swear I let out accidental shudders into the kiss tracing farther down his dick and the length of it. I wanted more so badly.

I continued running my fingers up and down his dick, kissing him feverishly with heavy breaths and his hand holding onto my boob, rolling his fingers over my nipple to force me to let out an occasional gasp and moans while we felt eachother up. Nothing made me hornier than when I could tell he was horny, and that he wanted me to do more to him.

I pushed my fingers against his dick with more pressure, letting them rub over the front of it and slip to the side. I wanted some sort of reaction from him. Not that I wasn't surprised he wasn't already crumbling under my touch from only grazing his tip over his pants with my thumb, but I wanted to earn that satisfaction of making him feel good.

I concentrated on the sounds of his breath hitching as we kissed and touched our tongues to the inside of eachothers mouths, looking for an indication of my effect on him. But this surprise would come to me in a different way.

My hand was still against his dick when I felt it pulse and slightly jump under my touch. My eyes widened for a moment in the kiss.

Eventually, we broke away. My gaze lingers on his lips and the shiny wet look of them for a moment before making contact with him.

'can i keep going?'

'yes' . He replied in such a way that was heavy, using a tone I had never heard from him before.

In that moment I became all too aware of our surroundings and realized we were still in my car, parked in broad daylight. I used it as an excuse out before I took things too far and couldn't stop myself.

'maybe.. not here?'

he paused, like he was looking around through the car windows for a second and laughed.

'hah yeah, probably not.' While shaking his head down at me and smiling. He had never been hotter.

I knew that things were going to be escalating much quicker soon, and I needed to be in control of it. It didn't matter how badly I wanted it, because my desire for things to be perfect was more important. Because I love him, and I want to be perfect, for him.